Hands down, for me this would have to be Transylvania by Night. Followed very closely by Jerusalem by Night. Both settings offered very rich character concepts that players would be excited to meet, as well as contained story seeds that were very interesting to explore.
It comes to no surprise that a huge majority of our Vampire: The Dark Ages games were set in Transylvania, and even those that were not (such as the Giovanni Chronicles, or this other game inspired by Joan of Arc set in France) would have major plots and story arcs that lead to the players travelling to this terrifying land.
Jerusalem, on the other hand, just felt amazing with its mysterious characters, its religious significance and its Modern Day role in the events of the coming Gehenna. My players still fondly recall the terrifying sight of seeing all the people who have trekked to Jerusalem in hopes of praying for salvation becoming the embodiment of the Malkavian Madness Network as Malkav reached out and took their corporeal forms to serve as vessels.
Ah yes. Great times indeed.
When it comes to NON-WRITTEN settings however, my favorite city to play in is New York City. The combination of rich and poor, of security and danger, of high rise towers and underground subways remains a delightful world to explore in a fictional way.
A huge majority of my games tend to use New York as our default setting. And admittedly, we embrace it for its fictional story potential far more than any real-world accuracy.
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